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A 1 : 1 : 1 co-crystal solvate formed between 1,8-dihydroxy-2,4,5,7-tetranitro-9,10-anthraquinone, dibenzothiophene and toluene (1), and a 1 : 1 co-crystal formed between 1,8-dihydroxy-2,4,5,7-tetranitro-9,10-anthraquinone and 4,6-dimethyldibenzothiophene (2) have been fully characterised. The molecular structures of the new and known coformer 1,8-dihydroxy-2,4,5,7-tetranitro-9,10- anthraquinone exhibit similar global features but differences in the orientations of the nitro substituents are evident. Also, in 1, the central ring of 1,8-dihydroxy-2,4,5,7- tetranitro-9,10-anthraquinone adopts a flattened half-chair conformation. Each of the remaining coformers are planar consistent with literature precedents. A common feature of the supramolecular aggregation in the crystal structures is the formation of stacks comprising alternating 1,8-dihydroxy- 2,4,5,7-tetranitro-9,10-anthraquinone and dibenzothiophene (or 4,6-dimethyldibenzothiophene in 2) molecules connected by π-π interactions. In 1, the central ring of 1,8-dihydroxy-2,4,5,7-tetranitro-9,10-anthraquinone does not form π-π interactions but in 2, it does, reflecting the different conformations of these rings. The new results are consistent with literature precedents of related p-rich dibenzothiophene co-crystals and suggest that the robust π-π synthons formed between these π-rich and π-deficient molecules may prove to be a useful strategy in deep desulfurization applications.

Co-crystals of 1,8-dihydroxy-2,4,5,7-tetranitro-9,10-anthraquinone with dibenzothiophene and 4,6-dimethyldibenzothiophene